Carlos Alcaraz fell to a defeat to fellow youngster Felix Auger-Aliassime in his first match as world number one.

Alcaraz triumphed at the US Open on Sunday, beating Casper Ruud to clinch his first grand slam title and, in the process, become the youngest world number one since the rankings were first published in 1973.

The 19-year-old is the second-youngest male player to win the title at Flushing Meadows in the Open Era, and only the third player since the majors welcomed professionals in 1968 to win the US Open title at his first or second main draw appearance after Arthur Ashe and Rod Laver (in the first two editions of the tournament).

Yet back on home soil in Spain on Friday, Alcaraz was unable to claim victory in his first match since becoming number one, as he went down 6-7 (3-7) 6-4 6-2 to Auger-Aliassime in the Davis Cup Finals.

Canada's Auger-Aliassime did not concede a break point as he dragged his country level in their tie with Spain in Valencia, teeing up a doubles decider after Roberto Bautista Agut defeated Vasek Pospisil 3-6 6-3 6-3.

Auger-Aliassime, 22, has won both of his career matches against Alcaraz, after defeating him in the US Open quarter-finals last year.

Britain's Jack Draper claimed one of the biggest scalps of the US Open so far after stunning sixth seed Felix Auger-Aliassime in a 6-4 6-4 6-4 victory to progress to the third round.

The 20-year-old defeated last year's Flushing Meadows semi-finalist to reach the last 32 in his first main-draw appearance at the final major of the season.

On the back of a second-round appearance at Wimbledon earlier this year, it represents Draper's best showing at a Grand Slam to date – and at few points did the Briton look at risk of letting the tie slip away from his grasp.

Draper saved all three of the break points he faced and took three of the 10 presented to him in a fine showing at Louis Armstrong Stadium.

For the Canadian, it brings a premature end to what the 22-year-old likely hoped would be a promising tournament that could have seen him go one better than last year.

He is the third top-10 seeded men's player to be eliminated, following first-round exits for Stefanos Tsitsipas and Taylor Fritz against qualifiers Daniel Elahi Galan and Brandon Holt respectively.

Nick Kyrgios' red-hot form has been halted after going down in three sets to eighth seed Hubert Hurkacz in the quarter-finals of the Canadian Open on Friday.

Hurkacz ran away with victory, triumphing 7-6 (7-4) 6-7 (5-7) 6-1 in one hour and 46 minutes in Montreal.

Wimbledon finalist Kyrgios had come into the encounter fresh from winning 15 of his past 16 matches, including lifting the title at last week's Washington Open. Kyrgios' run had fueled expectations around him at the upcoming US Open.

"Nick has been playing some incredible tennis throughout the past weeks, so it is a pleasure playing against him," Hurkacz said post-match in his on-court interview.

"I started really well. Nick was maybe a little bit injured, which might have hurt his serve. With both of us serving so well, that few per cent can make the difference."

Kyrgios was quick on serve but the 25-year-old Pole eventually ground him down, prevailing in the third set aided by an early break.

That break came after Kyrgios gave up two double faults, leading to the Australian to complain to the umpire about his opponent's mid-match break for a change of clothes.

The Australian was unable to break Hurkacz's serve throughout the match, with the Pole edging the aces count 20-19, while he was also superior on return. Kyrgios had more winners (55-47), but more unforced errors (24-13).

Hurkacz, who will face fourth seed Casper Ruud in the semi-finals, is the only former Masters 1000 champion left in the draw.

Ruud cruised into the last four with a 6-1 6-2 victory over hometown hero Felix Auger-Aliassime who was brushed aside in one hour and 14 minutes.

The Norwegian's win marks his third ATP Masters 1000 semi-final of the season, with the Canadian plagued by 21 unforced errors compared to Ruud's eight.

Unseeded Briton Daniel Evans fought back from a lopsided opening set to knock off Tommy Paul 1-6 6-3 6-4.

Evans will face Spaniard Pablo Carreno Busta after he defeated Jack Draper 7-6 (7-4) 6-1 in just under two hours.

Australia's Nick Kyrgios has now won 15 of his past 16 matches after defeating compatriot Alex de Minaur 6-2 6-3 in the third round of the Canadian Open – with his only loss coming in the Wimbledon final against Novak Djokovic.

Fresh off his first singles title since 2019 when he won last week's Washington Open, Kyrgios collected his ninth consecutive victory in impressive fashion, showing no difficulty in navigating his first-ever matchup against his fellow countryman.

He won the first four games of the match, and snatched a break in the first game of the second set to book his quarter-final against Poland's Hubert Hurkacz.

Hurkacz, the eighth seed, had to come back from a set down to defeat Spain's Albert Ramos-Vinolas 6-7 (6-8) 6-2 7-6 (7-3). He struggled with his serve early, with four double faults in the opening frame, but cleaned it up as the match went on, double-faulting only once in the last two sets.

England's top hope Cameron Norrie suffered a disappointing 6-3 6-4 defeat at the hands of world number nine Felix Auger-Aliassime, but Daniel Evans and Jack Draper made it through to fly the flag.

Evans pulled off an upset win to beat 10th seed Taylor Fritz 7-6 (7-5) 1-6 7-5, and 20-year-old Draper was up a set when 17th seed Gael Monfils retired with an injury at 6-2 0-2.

American Tommy Paul claimed another scalp with his 6-4 6-2 victory against 13th seed Marin Cilic, giving him back-to-back wins against top-15 opponents after emerging triumphant against Carlos Alcaraz in the previous round.

In the final match of the day, Pablo Carreno-Busta beat his third top-30 opponent of the week with a 6-2 6-4 result against Italy's Jannik Sinner, following strong successes against Matteo Berrettini and Holger Rune.

Nick Kyrgios started his Friday by finishing off his third-round win against Reilly Opelka, and his business was not finished until after 1am local time when he defeated Frances Tiafoe 6-7 (5-7) 7-6 (14-12) 6-2 in the quarter-final.

Due to length rain delays on Thursday, Kyrgios was one of five players forced to abandon their matches and return to finish them first thing on Friday, with Kyrgios and Russia's Andrey Rublev the only two to successfully navigate both.

Tiafoe defeated Botic van de Zandschulp 4-6 6-2 6-3 in the morning, but Kyrgios' ability to keep his service games short was a decisive factor, winning the ace count 35-14 and not conceding a single break all match.

Rublev had to deal with Maxime Cressy in the morning, winning 6-4 7-6 (10-8), setting up a quarter-final later at night against J.J. Wolf after the American defeated Holger Rune 7-5 4-6 6-3.

Rublev made his second match look far easier, cruising through 6-2 6-3 to earn a semi-final against Japan's Yoshihito Nishioka after he needed over three-and-a-half hours to beat Daniel Evans 7-6 (7-5) 4-6 7-5.

In an all-unseeded semi-final, Kyrgios will play Sweden's Mikael Ymer, who fought his way past Sebastian Korda 6-2 5-7 6-3 after the American beat Bulgaria's Grigor Dimitrov 4-6 6-1 6-2 earlier in the day.

Meanwhile, down in Mexico at the Los Cabos Open, Daniil Medvedev earned his spot in the final by defeating Serbia's Miomir Kecmanovic 7-6 (7-0) 6-1.

Medvedev will play England's Cameron Norrie for the title after he prevailed in arguably the match of the tournament against top-10 talent Felix Auger-Aliassime 6-4 3-6 6-3.

Daniil Medvedev showed on Thursday why he is the top overall seed at the Los Cabos Open, comfortably handling the challenge of Ricardas Berankis in a 6-2 6-2 win.

The world number one gave Berankis no avenues into the match, winning 48 per cent (27-of-56) of his total return points, while also converting 88 per cent (21-of-24) of his own successful first serves into points.

Medvedev will meet Serbia's Miomir Kecmanovic in the semi-final after he pulled off an impressive 6-2 6-4 victory against American Brandon Nakashima.

Kecmanovic's ability to serve his way out of trouble was the deciding factor, saving four of five break-point opportunities, while Nakashima could only save six out of 10.

Canada's Felix Auger-Aliassime booked his spot in the second semi-final after defeating America's Steve Johnson 6-4 7-6 (7-3).

The 22-year-old winner – who now sits ninth in the world rankings – served up 17 aces in the contest, while Johnson, who is usually known for his serve, could only muster four.

Cameron Norrie was a straights-sets winner over Radu Albot, although he needed a second-set tie-break to get the job done in a 6-3 7-6 (7-4) triumph.

Meanwhile, Norrie's British compatriot Daniel Evans won a war of attrition against American Taylor Fritz at the Washington Open, pulling ahead 3-6 7-6 (8-6) 4-1 before the heavy favourite retired due to the oppressive conditions.

With rising temperatures, combined with spots of rain, the humidity threatened to claim a number of scalps as multiple players in Thursday's action took extended medical timeouts, before a serious downpour halted the rest of play.

The only other matches to reach their conclusion were Yoshihito Nishioka's 7-6 (7-2) 7-6 (7-1) win against Karen Khachanov, and a 6-3 6-7 (3-7) 6-4 triumph for Sweden's Mikael Ymer against Finland's Emil Ruusuvuori.

When play resumes, Nick Kyrgios will look to finish off Reilly Opelka after reaching the rain with a 7-6 (7-1) 2-1 lead, and Grigor Dimitrov won his first set 6-4 against Sebastian Korda.

Botic van de Zandschulp was the beneficiary of the break against Frances Tiafoe, winning the first set 6-4 before slowing down in a big way to drop the second 6-2, but he will get a chance to recharge his batteries before the decider.

Second seed Hubert Hurkacz was a shock second-round casualty from the Citi Open on Wednesday after a straight-sets defeat to Emil Ruusuvuori.

World number 46 Ruusuvuori triumphed 6-4 7-6 (7-3) in one hour and 43 minutes to book a quarter-final spot.

Hurkacz, who is ranked 11th in the world and reached last year's Wimbledon semi-finals, fought hard but failed to capitalise on four break points throughout the match.

"He had an early break point, but then I was able to keep that service game and give myself a chance to break him and I was able to use it and then just try to keep my own serve," Ruusuvuori said.

"I just tried to hang in there and tried to stay as tough as [I] can."

Wimbledon runner-up Nick Kyrgios defeated 14th seed Tommy Paul 6-3 6-4 in one hour and 25 minutes.

The Australian hit 29-21 winners, with the majority coming from his serve and forehand, sending down 15 aces, winning 84 per cent on his first serve.

Kyrgios, who broke Paul in his opening service game, converted three of four break points for the match, while the American failed to capitalise on any of his four.

Sixth seed Denis Shapovalov was bundled out in the second round by American wildcard J.J. Wolf 6-2 6-7 (5-7) 6-3 in a major upset.

Third seed Taylor Fritz avoided an early exit with a 6-4 6-4 win over Australian Alexei Popyrin in one hour and 11 minutes, while fourth seed Reilly Opelka came from a set down to defeat Denis Kudla 6-7 (6-8) 6-4 6-4 in just over two hours. Opelka sent down 28 aces across the match.

Fifth seed Grigor Dimitrov got past Adrian Mannarino 6-1 3-6 7-5 and ninth seed Holger Rune brushed off Benoit Paire 6-3 6-2.

Francis Tiafoe defeated Christopher Eubanks 6-3 7-6 (7-2), while 13th seed Maxime Cressy fought back from an early deficit to get past Jack Sock 4-6 6-4 6-0 to set up a third-round clash with top seed Andrey Rublev.

There were defeats for 11th seed Alex de Minaur to Yoshihito Nishioka 3-6 7-6 (8-6) 6-2, 12th seed Sebastian Baez against Sebastian Korda 6-1 6-4 and 15th seed Aslan Karatsev against Andy Murray's first-round conqueror Mikael Ymer 6-4 3-6 6-4.

At the Los Cabos Open in Mexico, second seed Felix Auger-Aliassime had no troubles against local Juan Alejandro Hernandez Serrano, winning 6-3 7-5.

American sixth seed Brandon Nakashima also progressed into the quarter-finals with a 6-3 6-3 win over Max Purcell, while Miomir Kecmanovic beat Jordan Thompson 6-4 6-2.

Dominic Thiem declared he is "definitely back" after reaching the Swedish Open quarter-finals, while Hall of Fame Open favourite Felix Auger-Aliassime crashed out in the second round. 

Thiem earned his first tour-level win in 14 months by downing Emil Ruusuvuori on his Bastad debut, before reaching his first quarter-final of the season by overcoming Roberto Bautista Agut on Thursday.

The Austrian battled to a 7-6 (7-5) 3-6 6-4 victory over the fourth-seeded Bautista Agut, picking up his first top-20 win since beating Novak Djokovic at the ATP Finals in 2020.

Sebastian Baez, who defeated Alejandro Davidovich Fokina in straight sets, awaits in the next round and former world number three Thiem is ready for the task.

"The win against Emil gave me confidence that I can compete against the best players in the world and today against Roberto," said Thiem, the 2020 US Open champion.

"He is always such a tough opponent. I was expecting and hoping it would be a close match. Then when I won the first set in the tie-break I said 'Hey, I can win today.' 

"I had the belief until the end of the match and the third set was really good. It is a process. I beat Ruusuvuori and today I beat Bautista Agut.

"Two really top opponents, so if I can beat them I am definitely back. I am into the quarters of a really strong tournament, so I am happy. It is a process, but I am going the right way."

Second seed Andrey Rublev was made to work for his 7-5 4-6 7-6 (7-2) victory over Federico Coria and will meet Laslo Djere, who defeated Marc-Andrea Huesler in straight sets to reach the quarter-finals.

Meanwhile, Auger-Aliassime resumed his match with Jason Kubler in Newport that was suspended due to bad light on Wednesday with a slight advantage but fell to a 4-6 6-3 7-6 (7-4) second-round loss.

That marked a first top-10 victory for Kubler, continuing his fine 2022 season that saw him achieve his best major result at Wimbledon, where he reached the fourth round at the All England Club.

Fourth seed Maxime Cressy is yet to drop his serve at the tournament but needed to survive a first-set scare against fellow American Steve Johnson to triumph 6-7 (3-7) 6-4 6-4.

Second favourite John Isner will meet Cressy in the semi-finals after battling past fifth seed Benjamin Bonzi 6-7 (2-7) 7-6 (8-6) 7-6 (7-5).

Casper Ruud was a surprise second-round loser as the Swedish Open defending champion fell to Francisco Cerundolo, while the favourites battled through at the Hall of Fame Open.

Ruud, a French Open finalist and defending champion in Bastad , lacked his usual composure as world number 39 Cerundolo broke him three times to win 6-4 3-6 7-5 on Wednesday.

That marked a first top-10 career victory for Cerundolo after defeating world number five Ruud, guiding him to his first quarter-final appearance at the tournament.

"I'm feeling amazing, I'm really happy," said Cerundolo, whose previous best result was beating world number 24 Gael Monfils. "It's amazing getting my first Top 10 win. It's been the best year so far in my career.

"He's a French Open finalist and was the defending champion here, so it was a big challenge for me and I'm happy to go through."

Aslan Karatsev awaits in the quarter-finals Cerundolo after downing Frenchman Hugo Gaston 6-2 6-4.

Fifth seed Pablo Carreno Busta survived a first-set scare to defeat 2016 champion Albert Ramos-Vinolas 4-6 7-6 (7-5) 7-5.

The victory was Carreno Busta's 250th tour-level triumph and he will next face third favourite Diego Schwartzman, who overcame Elias Ymer in straight sets.

Third seed Alexander Bublik was made to work for a 6-3 3-6 6-2 second-round victory over Jack Sock in Newport and Andy Murray edged past Wimbledon doubles champion Max Purcell.

Murray needed almost two-and-a-half hours to get the better of Purcell, eventually triumphing 4-6 6-2 6-1 to tee up a last-eight meeting with Bublik.

Fourth favourite Maxime Cressy had little trouble in beating fellow American Mitchell Krueger 6-3 6-4 and will next face Steve Johnson, who progressed past seventh seed Jiri Vesely with a walkover.

Benjamin Bonzi, ranked as fifth seed in the United States, eased past Christopher Eubanks in straight sets, while James Duckworth triumphed 7-5 3-6 6-2 over Quentin Halys.

John Isner joined the list of favourites who made the third round in routine fashion, beating Peter Gojowczyk in straight sets 6-3 7-6 (8-6), before top seed Felix Auger-Aliassime faced some adversity against Jason Kubler following the Australian's strong run into the fourth round of Wimbledon.

Auger-Aliassime has a slight advantage, leading 6-4 3-6 6-5 before play was suspended due to poor light. When play resumes, Kubler will serve with a chance to force a third-set tiebreak.

Novak Djokovic has slipped to seventh in the ATP Tour rankings despite winning Wimbledon, where ranking points were stripped in this year's tournament.

Players from Russia and Belarus were banned from competing at the third major of the year due to the ongoing invasion of Ukraine.

The ATP and WTA retaliated by stripping ranking points from the event at the All England Club, where the likes of world number one Daniil Medvedev and Andrey Rublev did not feature.

Moscow-born Elena Rybakina, who switched to represent Kazakhstan four years ago, lifted the women's title in the singles competition, while Djokovic triumphed for a fourth straight time in the men's event.

Yet, Djokovic has lost 2,000 rankings points – the standard total awarded to a grand slam singles champion – after winning in SW19 last year, with no such rewards available on this occasion.

That meant the Serbian has dropped from third place to seventh, his lowest position since August 2018 when he fell to 10th.

Djokovic moved within just one major title of Rafael Nadal's record of 22 grand slams, and the Spaniard has jumped up one spot to third.

Medvedev and Alexander Zverev are unmoved as the respective top two after losing just 180 rankings points in the latest edition. Both missed Wimbledon, with the Russian banned and the German still injured.

Stefanos Tsitsipas, Casper Ruud and Carlos Alcaraz make up the top six after climbing a place each, while Rublev, Felix Auger-Aliassime and Jannik Sinner are the trio behind Djokovic.

Nick Kyrgios appeared in his maiden major final against Djokovic at Wimbledon as world number 40, the lowest-ranked grand slam male finalist since Marcos Baghdatis (54) at the Australian Open in 2006.

Just a day later Kyrgios has dropped five places to 45th in the rankings, losing 90 points from his third-round berth last year. If the ban was not imposed, the Australian would have broken into the top 20.

Cameron Norrie is another loser from the ranking points fallout. His run to the semi-finals at the London major would have seen him climb to eighth, but instead he has to settle for 11th.

A spirited fightback from Nick Kyrgios saw the Australian beat second seed Stefanos Tsitsipas in the Halle Open on Wednesday.

Kyrgios suffered a disappointing semi-final defeat to Andy Murray in Stuttgart last week, but looked greatly improved against Tsitsipas as he recovered from a set down to win 5-7 6-2 6-4.

It was the second serve of both men where Kyrgios shone, winning 76 per cent (28 of 37) of points on his second serve, and 58 per cent (23 of 40) on his opponent's.

"Stef is one of the best players in the world at the moment and he's going to have some amazing results and I'm sure many, many grand slams," Kyrgios said following his win.

"I don't know if I can say the same for me, but I'm happy to still be able to produce this level with the tournaments I play. It is a testament to how hard I do work when I'm not playing."

He will face Pablo Carreno Busta in the quarter-finals after the Spanish sixth seed beat Sebastian Korda 6-4 0-6 6-3.

Elsewhere, Hubert Hurkacz will face Felix Auger-Aliassime in the last eight after defeating Ugo Humbert 7-6 (7-5) 6-3, while the Canadian also won in straight sets against Mackenzie McDonald 7-6 (9-7) 6-1.

The one remaining first round match saw number one seed Daniil Medvedev beat David Goffin 6-3 6-2 to set up a second round clash with Ilya Ivashka.

At the Queen's Club Championships, sixth seed Denis Shapovalov was eliminated by Tommy Paul 6-4 2-6 6-4, with the American now scheduled to face Stanislas Wawrinka in the second round.

It means that six of the eight seeds in west London were knocked out in the first round, with Matteo Berrettini and Marin Cilic the only remaining seeds. The latter sealed his place in the quarter-finals on Wednesday with a 7-6 (8-6) 7-5 win over Alexander Bublik.

Cilic will play Finland's Emil Ruusuvuori in the last eight after he beat home favourite Jack Draper 6-2 7-6 (7-2).

The best contest of the day came between Alejandro Davidovich Fokina and Alex de Minaur, with the former coming from behind to win 4-6 6-4 7-5 to set up a quarter-final with Botic van de Zandschulp, who beat Grigor Dimitrov 7-6 (7-5) 6-3.

Daniil Medvedev is one match away from winning his first title of 2022 after beating Adrian Mannarino in straight sets to reach the Rosmalen Grass Court Championships final.

Defending champion Mannarino had won eight matches in a row at the ATP 250 event, which was last held in 2019, but he fell 7-5 7-5 to Medvedev in a match lasting a little under two hours.

Top seed Medvedev, whose most recent appearance in a final came at the Australian Open in January, will now face home favourite Tim van Rijthoven on Sunday.

"Adrian plays good, and some games in this match I was like: okay, I can't do anything," said Medvedev, who will reclaim top spot in the ATP rankings next week.

"I had to just continue playing my tennis. He was unbelievable sometimes, missing sometimes, so I just continued my game, and it managed to work today."

Medvedev was far from his best against flat-hitting Mannarino, with the first set featuring five breaks of serve, but the 26-year-old did enough to edge in front.

After wasting a chance to serve out the match in the 10th game of the second set, Medvedev edged a mammoth 11th game and avoided any sort of scare to advance through.

The Russian will next face a different sort of test against Van Rijthoven after the Dutch wildcard stunned second seed Felix Auger-Aliassime earlier on Saturday.

Van Rijthoven, who had not won a match at tour level until his opening-round win over Matthew Ebden, prevailed 6-3 1-6 7-6 (7-5) in a thrilling semi-final.

After sharing the first two sets, Van Rijthoven wasted six break-point opportunities in the decider, but he held his nerve in the tie-break to keep his dream run going.

He is the first Dutchman to reach the final in 's-Hertogenbosch since Raemon Sluiter in 2009.

Andy Murray claimed his first win over a top-five opponent since 2016 as he stunned Stefanos Tsitsipas to reach the Stuttgart Open semi-finals.

Murray started his preparations for the grass-court swing with a run to the semi-finals of the challenger at Surbiton.

He knocked off seventh seed Alexander Bublik to reach the last eight in Stuttgart but a meeting with the top seed and world number five represented a much more imposing challenge.

It was one the two-time Wimbledon champion rose to emphatically, winning a first-set tie-break and then claiming the second set in comfortable fashion to cement a 7-6 (7-4) 6-3 win, gaining revenge for his contentious five-set defeat to the Greek at last year's US Open.

Murray's previous win over a top-five opponent came in the ATP Finals six years ago, when he defeated Novak Djokovic in a year that also saw him win Wimbledon.

"I thought I did well. He served unbelievably in the first set," Murray said in his on-court interview.

"I felt like I had very few chances, but when he was creating chances on my serve, I stayed strong.

"I played a really solid tie-break and in the second set, once I was in the rallies, I felt like I was dictating a lot of the points. It was a good performance."

Murray is up to 53rd in the live ATP rankings and is bidding to get back into the top 50 for the first time since 2018. 

Standing between him and a place in the final is Nick Kyrgios, who was 7-6 (7-3) 3-0 up when Marton Fucsovics retired from their quarter-final clash.

Matteo Berrettini beat Lorenzo Sonego in three sets, while Oscar Otte won by walkover against Benjamin Bonzi.

At the Rosmalen Grass Court Championships in 's-Hertogenbosch, Daniil Medvedev saw off Ilya Ivashka 7-6 (10-8) 6-4.

Medvedev, who will soon return to world number one when the ranking points from the French Open come into effect, sees the grass-court season as a chance to cement his grip on that spot.

"I don't have many points to defend on grass and I have some to win, so hopefully I can play well, starting here," said Medvedev. "Every round is points and the higher you get, the more you need to step up."

He will face defending champion Adrian Mannarino in the semi-finals, while second seed Felix Auger-Aliassime is into a last-four clash with home hope Tim van Rijthoven after beating Karen Khachanov. 

Daniil Medvedev started his grass-court season with victory over Gilles Simon in the Rosmalen Grass Court Championships, while Hubert Hurkacz and Denis Shapovalov suffered shock defeats in Stuttgart.

Medvedev will replace Novak Djokovic at the top of the rankings next Monday and the Russian could celebrate by claiming a first title of the year in ‘s-Hertogenbosch.

The top seed, who will not compete at Wimbledon due to a ban on Russian and Belarusian players, beat Frenchman Simon 7-5 6-4 on Thursday after saving three set points and storming back from 5-2 down in the opener, setting up a quarter-final against lya Ivashka.

Felix Auger-Aliassime, the second seed, defeated Tallon Griekspoor 7-6 (7-2) 7-6 (7-5), but third seed Taylor Fritz was beaten by wildcard Tim van Rijthoven in straight sets.

Alex de Minaur and Jenson Brooksby also made early exits, losing to French duo Adrian Mannarino and Hugo Gaston respectively.

Marton Fucsovics claimed the scalp of third seed Hurkacz to reach the last 16 at the Stuttgart Open, winning 7-5 6-7 (7-) 6-3

Shapovalov also lost his opening of the grass-court season, Oscar Otte getting the better of the fourth seed 7-6 (8-6) 7-6 (7-4)

There was no such trouble for top seed Stefanos Tsitsipas, who beat Dominic Stricker 6-3 6-4, and Andy Murray accounted for seventh seed Alexander Bublik in straight sets.